Reese Witherspoon, Vanity Fair Oscar Party

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America's Sweetheart has a bit of naughty side.

Reese Witherspoon showed some major cleavage—and plenty of side-boob, too—when she made an appearance at Vanity Fair's annual Oscar party Sunday. The Wild star's Jason Wu for Hugo Boss dress was a departure for the actress, who typically favors more classic and conservative red carpet styles.

The Walk the Line star, who won an Oscar in 2006, accessorized with Irene Neuwirth jewels. She also congratulated Best Actor winner Matthew McConaughey, her costar in Mud and her agent husband Jim Toth's client. "A stunning performance, an amazing night!" the 37-year-old wrote on WhoSay.

Witherspoon, of course, wasn't the only woman who brought some sex appeal to the Vanity Fair party.

Miranda Kerr, Vanity Fair Oscar Party

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Miranda Kerrshimmered in a silver floor-length gown that featured a plunging neckline. Dazzling diamond jewelry, courtesy of Jacob & Co., offset the 30-year-old Australian supermodel's risqué look.

Gabrielle Union, Vanity Fair Oscar Party

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Fellow partygoer Gabrielle Union also got the cleavage memo, rocking a daring and décolletage-baring gown at the star-studded soiree. The belted design featured a sheer black skirt with cascading sequined strips. Naturally, the 41-year-old Being Mary Jane star was on trend with a berry lip color.

Who was your best-dressed actress at Vanity Fair's Oscar party? Sound off in the comments below!

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